@Jordan Tinning - Please message me with the answers to my follow up post above until I am unspammed by BP to get started.

It remains to be seen whether or not this law passes or another like it, but whereas we were at one point heavily-considering a second rental property here, we're holding off until we get a clearer sense as to how this will pan out.

Many ways that pans out but overall "condo model" in terms of what you're describing, either way. 

Buy and hold in Hawaii doesn't usually pan out unless you're willing to go negative monthly (often considerably) to maybe gain some appreciation over time.

With the 1031 exchange it sounds like i could start it and then if it doesnt pan out im at the same point as original and just pay taxes in 2025 on the capital gains.  

If the trust is what is called a "disregarded entity" (meaning it does not have it's own TIN and does not file a tax return) then the activity of that property is reported on your personal tax return. 

That's the kicker with class D - looks good on paper, doesn't pan out that way in real life True that.Paper returns are always different to real life returns.We also never calculate our time and risk as they aren't tangible estimates.D class comes with a lot of time and risk associated with it.And PM needs to be really rough in order to make it work.

What is your game pan for the property and how do you propse to make the monthly payments?

If discussing a different business operation, say buying a restaurant, immediately people won't think the value is just the market value of the location, the tables, the broiler, dishwasher, plates, pots and pans, right.

I'm ready and willing to work harder to achieve my goals, but not gonna lie, I have to accept the probability it may not pan out, too.